ethyl 1,2-dihydro-6-methyl-2-oxo-4-(2-phenylethyl)pyrimidine-5-carboxylate | 1123495-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 1,2-dihydro-6-methyl-2-oxo-4-(2-phenylethyl)pyrimidine-5-carboxylate
• 英文别名: ethyl 6-methyl-4-(1-phenylethyl)-2-oxo-1,2-dihydropyrimidine-5-carboxylate；Ethyl 6-methyl-4-(2-phenylethyl)pyrimidin-2(1h)-one-5-carboxylate；ethyl 6-methyl-2-oxo-4-(2-phenylethyl)-1H-pyrimidine-5-carboxylate
• CAS: 1123495-65-7
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: NUBSULCDKSXSAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5‑ethoxycarbonyl‑4‑(2‑phenylethyl)‑6‑methyl‑3,4‑dihydropyrimidin‑2(1H)‑one 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 以63%的产率得到ethyl 1,2-dihydro-6-methyl-2-oxo-4-(2-phenylethyl)pyrimidine-5-carboxylate
  参考文献：
  名称：

  Biginelli 反应产物的氧化：2-未取代的 1,4-二氢嘧啶、嘧啶和 2-羟基嘧啶的合成

  摘要：

  我们设计了一条从 Biginelli 产物二氢嘧啶-2(1H)-硫酮获得 2-未取代嘧啶衍生物的新途径，分两步进行： 在湿氧化铝或过氧化氢存在下使用 oxone 氧化二氢嘧啶-2(1H)-硫酮催化量的硫酸氧钒提供1,4-二氢嘧啶，通过KMnO 4 的处理将其进一步氧化为2-未取代的嘧啶。KMnO 4 氧化二氢嘧啶-2(1H)-酮以优异的产率形成2-羟基嘧啶，而尝试通过KMnO 4 直接脱硫二氢嘧啶-2(1H)-硫酮导致形成2-羟基嘧啶，相同的产物由二氢嘧啶-2(1H)-one氧化得到。

  DOI：

  10.1055/s-0028-1087920

文献信息

• Oxidation of Biginelli Reaction Products: Synthesis of 2-Unsubstituted 1,4-Dihydropyrimidines, Pyrimidines, and 2-Hydroxypyrimidines
  作者：Hyunik Shin、Sam Kim、Bo Choi、Jae Lee、Ki Lee、Tae Lee、Young Kim

  DOI：10.1055/s-0028-1087920

  日期：2009.3

  from the Biginelli product, dihydropyrimidin-2(1H)-thiones in two steps: Oxidation of dihydropyrimidin-2(1H)-thiones using oxone on wet alumina or hydrogen peroxide in the presence of catalytic amount of vanadyl sulfate provided 1,4-di-hydropyrimidine, which was further oxidized to 2-unsubstituted pyrimidines by the treatment of KMnO 4 . Oxidation of dihydropyrimidin-2(1H)-ones by KMnO 4 formed 2-hydroxypyrimidine

  我们设计了一条从 Biginelli 产物二氢嘧啶-2(1H)-硫酮获得 2-未取代嘧啶衍生物的新途径，分两步进行： 在湿氧化铝或过氧化氢存在下使用 oxone 氧化二氢嘧啶-2(1H)-硫酮催化量的硫酸氧钒提供1,4-二氢嘧啶，通过KMnO 4 的处理将其进一步氧化为2-未取代的嘧啶。KMnO 4 氧化二氢嘧啶-2(1H)-酮以优异的产率形成2-羟基嘧啶，而尝试通过KMnO 4 直接脱硫二氢嘧啶-2(1H)-硫酮导致形成2-羟基嘧啶，相同的产物由二氢嘧啶-2(1H)-one氧化得到。
• Light-induced Free Radical Oxidation of 2-Oxo-1,2,3,4-tetrahydropyrimidines
  作者：Hamid Reza Memarian、Leila Hejazi、Asadallah Farhadi

  DOI：10.1515/znb-2012-0313

  日期：2012.3.1

  A variety of 4-substituted 5-acetyl- and 5-carboethoxy-2-oxo-1,2,3,4-tetrahydropyrimidines were oxidized under UV irradiation in the presence or absence of benzoyl peroxide. The nature of the substituents on the 4- and 5-positions of the heterocyclic ring affects the rate of photo-oxidation, and irradiation of these compounds in the presence of benzoyl peroxide decreases the time of reaction drastically. Removal of 4-H by a benzoyloxy radical under formation of a trihydropyrimidinoyl radical intermediate occurs in the rate-determining step. The stability of this benzylic and allylic radical intermediate is affected by the nature and the position of the additional substituent on the phenyl group located at C-4.

  一系列4-取代的5-乙酰基和5-羧乙酯基-2-氧代-1,2,3,4-四氢嘧啶在紫外辐射下在有或无苯甲酰过氧化物存在下被氧化。杂环环上4-和5-位置的取代基的性质影响光氧化的速率，这些化合物在有苯甲酰过氧化物存在下的照射显著减少了反应时间。在速率决定步骤中，苯甲酰氧自由基去除4-H形成三氢嘧啶基自由基中间体。这种苄基和烯丙基自由基中间体的稳定性受到苯基团上附加取代基的性质和位置的影响，该苯基团位于C-4。
• Klingebiel, Uwe; Matthes, Christoph; Ringe, Arne, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2009, vol. 64, # 5, p. 532 - 540
  作者：Klingebiel, Uwe、Matthes, Christoph、Ringe, Arne、Magull, Joerg

  DOI：——

  日期：——
• Light-induced dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones
  作者：Hamid Reza Memarian、Asadollah Farhadi

  DOI：10.1007/s00706-009-0156-0

  日期：2009.10

  UV light irradiation of Biginelli 3,4-dihydropyrimidin-2(1H)-ones in chloroform in an argon atmosphere leads to dehydrogenation of these compounds to their corresponding pyrimidin-2(1H)-ones in excellent yields. Irradiation in the same solvent under an oxygen atmosphere generates, in addition, various hitherto unidentified products. A light-induced electron transfer from the substrate to the solvent is proposed as the initial event, supported by the detection of dichloromethane and hydrogen chloride in the photolysate.
• Free-radical oxidation of 1,2,3,4-tetrahydro-2-oxopyrimidines
  作者：Hamid Reza Memarian、Nazanin Jafarpour、Asadallah Farhadi

  DOI：10.1007/s00706-011-0573-8

  日期：2012.2

  Free-radical oxidation of 4-substituted 5-acetyl- and 5-carboethoxy-1,2,3,4-tetrahydro-2-oxopyrimidines using benzoyl peroxide under thermal conditions has been investigated to elucidate the effects of the nature of the substituents in the 4- and 5-positions on the rate of reaction. Whereas the presence of the acetyl group instead of the carboethoxy group in position 5 decreases the rate of oxidation, the nature of the additional substituent (electron-releasing or electron-withdrawing group) and also its location on the phenyl ring attached to C-4 of the tetrahydropyrimidinone ring effectively influence the rate of reaction. The latter observation supports the proposal that the removal of the 4-hydrogen on the heterocyclic ring occurs in the rate-determining step.